Triethylamine → HCID 69982214, compound

Participants

Reaction Steps

3-(4-((3R)-3-Hydroxy-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one (700 mg, 1.9 mmol) was dissolved in DMSO(5 ml) under nitrogen and triethylamine (2.03 g, 20 mmol) added. A solution of sulfur trioxide pyridine complex (0.95 g, 6 mmol) in DMSO(5 ml) was added dropwise over 20 minutes. After stirring 1 hour at ambient temperature, the mixture was diluted with water (100 ml) and extracted into EtOAc (150 ml). The organics were washed with water (2×50 ml), brine (50 ml) and dried (magnesium sulfate). After evaporation, the residue was purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 3% MeOH in dichloromethane. Relevant fractions were combined and evaporated, and the residue crystallised from ethanol (35 ml) to give product (176 mg). MS (ESP): 362 (MH+) for C17H16FN3O5.

Provenance & Evidence